# Supplementary Information (SI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2026

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
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#######################################################################

data_mo_VA214_0m
_database_code_depnum_ccdc_archive 'CCDC 2480463'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2025-08-14 deposited with the CCDC.	2026-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H14 F2 N2 O, C H Cl3'
_chemical_formula_sum            'C25 H15 Cl3 F2 N2 O'
_chemical_formula_weight         503.74

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.474(4)
_cell_length_b                   13.727(4)
_cell_length_c                   12.998(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.823(12)
_cell_angle_gamma                90
_cell_volume                     2261.6(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9487
_cell_measurement_theta_min      2.187
_cell_measurement_theta_max      28.2015

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.479
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.102
_exptl_absorpt_coefficient_mu    0.443
_shelx_estimated_absorpt_T_min   0.909
_shelx_estimated_absorpt_T_max   0.956
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6071
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS 3.0'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III C14'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.391
_diffrn_reflns_number            28966
_diffrn_reflns_av_unetI/netI     0.0469
_diffrn_reflns_av_R_equivalents  0.0627
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.187
_diffrn_reflns_theta_max         28.296
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5595
_reflns_number_gt                4411
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX5 (Bruker, 2023)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0638P)²+0.5545P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5595
_refine_ls_number_parameters     326
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0453
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1173
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.53924(12) 0.39538(11) 0.13906(12) 0.0357(3) Uani 1 1 d . . . . .
H1 H 0.476635 0.366926 0.090371 0.043 Uiso 1 1 calc R U . . .
C2 C 0.60735(13) 0.44354(12) 0.09851(13) 0.0409(3) Uani 1 1 d . . . . .
H2 H 0.591622 0.447507 0.021647 0.049 Uiso 1 1 calc R U . . .
C3 C 0.69940(13) 0.48682(13) 0.16839(14) 0.0431(4) Uani 1 1 d . . . . .
H3 H 0.746064 0.519346 0.139066 0.052 Uiso 1 1 calc R U . . .
C4 C 0.72224(12) 0.48220(11) 0.27964(13) 0.0377(3) Uani 1 1 d . . . . .
H4 H 0.784046 0.513031 0.326850 0.045 Uiso 1 1 calc R U . . .
C5 C 0.65508(10) 0.43227(10) 0.32462(11) 0.0301(3) Uani 1 1 d . . . . .
C6 C 0.56242(10) 0.38812(10) 0.25375(11) 0.0298(3) Uani 1 1 d . . . . .
C7 C 0.49465(10) 0.33642(10) 0.29931(11) 0.0286(3) Uani 1 1 d . . . . .
C8 C 0.40055(11) 0.28778(11) 0.23457(12) 0.0350(3) Uani 1 1 d . . . . .
H8 H 0.380034 0.288370 0.157059 0.042 Uiso 1 1 calc R U . . .
C9 C 0.34094(11) 0.24102(12) 0.28385(13) 0.0372(3) Uani 1 1 d . . . . .
H9 H 0.278848 0.207979 0.240608 0.045 Uiso 1 1 calc R U . . .
C10 C 0.37029(10) 0.24046(10) 0.40192(12) 0.0323(3) Uani 1 1 d . . . . .
C11 C 0.61283(10) 0.37346(9) 0.48222(11) 0.0277(3) Uani 1 1 d . . . . .
C12 C 0.67830(10) 0.42333(10) 0.44100(11) 0.0289(3) Uani 1 1 d . . . . .
C13 C 0.77540(10) 0.47074(10) 0.51710(11) 0.0307(3) Uani 1 1 d . . . . .
C14 C 0.87294(11) 0.42580(12) 0.54256(14) 0.0406(3) Uani 1 1 d . . . . .
H14 H 0.878200 0.363747 0.512462 0.049 Uiso 1 1 calc R U . . .
C15 C 0.96287(12) 0.47103(13) 0.61176(15) 0.0464(4) Uani 1 1 d . . . . .
H15 H 1.029736 0.440131 0.630187 0.056 Uiso 1 1 calc R U . . .
C16 C 0.95360(12) 0.56070(13) 0.65292(14) 0.0447(4) Uani 1 1 d . . . . .
C17 C 0.85871(14) 0.60785(13) 0.62936(17) 0.0509(4) Uani 1 1 d . . . . .
H17 H 0.854428 0.670091 0.659523 0.061 Uiso 1 1 calc R U . . .
C18 C 0.76918(12) 0.56195(12) 0.56017(15) 0.0440(4) Uani 1 1 d . . . . .
H18 H 0.702688 0.593497 0.542089 0.053 Uiso 1 1 calc R U . . .
C19 C 0.63669(10) 0.35883(10) 0.60228(11) 0.0285(3) Uani 1 1 d . . . . .
C20 C 0.72175(11) 0.30041(11) 0.65969(12) 0.0332(3) Uani 1 1 d . . . . .
H20 H 0.760673 0.267418 0.621533 0.040 Uiso 1 1 calc R U . . .
C21 C 0.75044(12) 0.28979(11) 0.77261(12) 0.0377(3) Uani 1 1 d . . . . .
H21 H 0.808980 0.250456 0.812091 0.045 Uiso 1 1 calc R U . . .
C22 C 0.69216(13) 0.33748(11) 0.82552(12) 0.0389(3) Uani 1 1 d . . . . .
C23 C 0.60670(14) 0.39525(12) 0.77154(13) 0.0418(3) Uani 1 1 d . . . . .
H23 H 0.567463 0.427025 0.810207 0.050 Uiso 1 1 calc R U . . .
C24 C 0.57941(12) 0.40579(11) 0.65876(12) 0.0365(3) Uani 1 1 d . . . . .
H24 H 0.520977 0.445529 0.619941 0.044 Uiso 1 1 calc R U . . .
N1 N 0.51951(8) 0.33092(8) 0.41008(9) 0.0271(2) Uani 1 1 d . . . . .
N2 N 0.46098(9) 0.28564(9) 0.46311(10) 0.0311(2) Uani 1 1 d . . . . .
O1 O 0.31547(8) 0.20049(8) 0.45086(9) 0.0390(2) Uani 1 1 d . . . . .
F1 F 1.04182(8) 0.60567(9) 0.71993(10) 0.0655(3) Uani 1 1 d . . . . .
F2 F 0.71863(10) 0.32664(8) 0.93572(8) 0.0560(3) Uani 1 1 d . . . . .
C25 C 0.12033(13) 0.15133(14) 0.50210(16) 0.0498(4) Uani 1 1 d . U . . .
H25 H 0.177900 0.194677 0.496426 0.060 Uiso 1 1 calc R U . A 1
Cl1 Cl 0.0321(5) 0.1304(5) 0.3685(5) 0.0775(11) Uani 0.57(3) 1 d . U P B 1
Cl2 Cl 0.0503(6) 0.2153(7) 0.5692(5) 0.0897(14) Uani 0.57(3) 1 d . U P B 1
Cl3 Cl 0.1792(5) 0.0502(3) 0.5799(4) 0.0685(10) Uani 0.57(3) 1 d . U P B 1
Cl1D Cl 0.0379(8) 0.1167(9) 0.3728(8) 0.0884(19) Uani 0.43(3) 1 d . U P B 2
Cl2D Cl 0.0622(6) 0.2298(7) 0.5780(6) 0.0759(12) Uani 0.43(3) 1 d . U P B 2
Cl3D Cl 0.1568(11) 0.0394(7) 0.5684(8) 0.103(2) Uani 0.43(3) 1 d . U P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.373(2) . ?
C1 C6 1.419(2) . ?
C1 H1 0.9500 . ?
C2 C3 1.397(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.374(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.411(2) . ?
C4 H4 0.9500 . ?
C5 C6 1.4122(19) . ?
C5 C12 1.442(2) . ?
C6 C7 1.4335(19) . ?
C7 N1 1.3652(18) . ?
C7 C8 1.4275(19) . ?
C8 C9 1.348(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.449(2) . ?
C9 H9 0.9500 . ?
C10 O1 1.2531(18) . ?
C10 N2 1.3606(18) . ?
C11 C12 1.3617(19) . ?
C11 N1 1.4148(17) . ?
C11 C19 1.4962(19) . ?
C12 C13 1.4953(19) . ?
C13 C18 1.386(2) . ?
C13 C14 1.386(2) . ?
C14 C15 1.387(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.365(3) . ?
C15 H15 0.9500 . ?
C16 F1 1.3603(18) . ?
C16 C17 1.372(2) . ?
C17 C18 1.387(2) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C19 C20 1.3905(19) . ?
C19 C24 1.391(2) . ?
C20 C21 1.393(2) . ?
C20 H20 0.9500 . ?
C21 C22 1.373(2) . ?
C21 H21 0.9500 . ?
C22 F2 1.3618(17) . ?
C22 C23 1.378(2) . ?
C23 C24 1.393(2) . ?
C23 H23 0.9500 . ?
C24 H24 0.9500 . ?
N1 N2 1.3609(16) . ?
C25 Cl2 1.726(5) . ?
C25 Cl1D 1.737(10) . ?
C25 Cl3 1.742(5) . ?
C25 Cl3D 1.748(7) . ?
C25 Cl1 1.764(7) . ?
C25 Cl2D 1.809(7) . ?
C25 H25 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 119.96(14) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C1 C2 C3 121.12(14) . . ?
C1 C2 H2 119.4 . . ?
C3 C2 H2 119.4 . . ?
C4 C3 C2 119.81(14) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 120.82(14) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C4 C5 C6 119.19(13) . . ?
C4 C5 C12 122.32(13) . . ?
C6 C5 C12 118.48(12) . . ?
C5 C6 C1 119.08(13) . . ?
C5 C6 C7 119.28(12) . . ?
C1 C6 C7 121.64(13) . . ?
N1 C7 C8 116.56(12) . . ?
N1 C7 C6 120.01(12) . . ?
C8 C7 C6 123.43(13) . . ?
C9 C8 C7 119.73(14) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C10 120.88(13) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
O1 C10 N2 118.03(13) . . ?
O1 C10 C9 122.94(13) . . ?
N2 C10 C9 119.03(13) . . ?
C12 C11 N1 119.70(12) . . ?
C12 C11 C19 122.62(12) . . ?
N1 C11 C19 117.66(11) . . ?
C11 C12 C5 121.09(12) . . ?
C11 C12 C13 119.79(12) . . ?
C5 C12 C13 119.12(12) . . ?
C18 C13 C14 119.21(13) . . ?
C18 C13 C12 120.08(12) . . ?
C14 C13 C12 120.68(13) . . ?
C13 C14 C15 120.31(15) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C16 C15 C14 118.82(15) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
F1 C16 C15 118.95(15) . . ?
F1 C16 C17 118.34(16) . . ?
C15 C16 C17 122.71(15) . . ?
C16 C17 C18 118.05(16) . . ?
C16 C17 H17 121.0 . . ?
C18 C17 H17 121.0 . . ?
C13 C18 C17 120.91(15) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
C20 C19 C24 119.20(13) . . ?
C20 C19 C11 118.92(12) . . ?
C24 C19 C11 121.80(12) . . ?
C19 C20 C21 120.64(14) . . ?
C19 C20 H20 119.7 . . ?
C21 C20 H20 119.7 . . ?
C22 C21 C20 118.46(14) . . ?
C22 C21 H21 120.8 . . ?
C20 C21 H21 120.8 . . ?
F2 C22 C21 118.98(14) . . ?
F2 C22 C23 118.29(15) . . ?
C21 C22 C23 122.72(14) . . ?
C22 C23 C24 118.19(14) . . ?
C22 C23 H23 120.9 . . ?
C24 C23 H23 120.9 . . ?
C19 C24 C23 120.78(14) . . ?
C19 C24 H24 119.6 . . ?
C23 C24 H24 119.6 . . ?
N2 N1 C7 125.62(11) . . ?
N2 N1 C11 112.97(11) . . ?
C7 N1 C11 121.41(11) . . ?
C10 N2 N1 118.16(12) . . ?
Cl2 C25 Cl3 109.4(2) . . ?
Cl1D C25 Cl3D 102.5(8) . . ?
Cl2 C25 Cl1 106.2(4) . . ?
Cl3 C25 Cl1 117.6(4) . . ?
Cl1D C25 Cl2D 116.0(5) . . ?
Cl3D C25 Cl2D 110.8(3) . . ?
Cl2 C25 H25 107.8 . . ?
Cl3 C25 H25 107.8 . . ?
Cl1 C25 H25 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.6(2) . . . . ?
C1 C2 C3 C4 -0.6(2) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C3 C4 C5 C6 -1.1(2) . . . . ?
C3 C4 C5 C12 178.01(14) . . . . ?
C4 C5 C6 C1 -0.13(19) . . . . ?
C12 C5 C6 C1 -179.28(12) . . . . ?
C4 C5 C6 C7 179.31(13) . . . . ?
C12 C5 C6 C7 0.17(18) . . . . ?
C2 C1 C6 C5 1.0(2) . . . . ?
C2 C1 C6 C7 -178.44(13) . . . . ?
C5 C6 C7 N1 0.54(19) . . . . ?
C1 C6 C7 N1 179.96(12) . . . . ?
C5 C6 C7 C8 -178.68(12) . . . . ?
C1 C6 C7 C8 0.7(2) . . . . ?
N1 C7 C8 C9 1.0(2) . . . . ?
C6 C7 C8 C9 -179.78(13) . . . . ?
C7 C8 C9 C10 0.8(2) . . . . ?
C8 C9 C10 O1 177.74(14) . . . . ?
C8 C9 C10 N2 -1.9(2) . . . . ?
N1 C11 C12 C5 -1.06(19) . . . . ?
C19 C11 C12 C5 177.19(12) . . . . ?
N1 C11 C12 C13 178.28(11) . . . . ?
C19 C11 C12 C13 -3.47(19) . . . . ?
C4 C5 C12 C11 -179.01(13) . . . . ?
C6 C5 C12 C11 0.11(19) . . . . ?
C4 C5 C12 C13 1.6(2) . . . . ?
C6 C5 C12 C13 -179.23(12) . . . . ?
C11 C12 C13 C18 -83.14(18) . . . . ?
C5 C12 C13 C18 96.21(17) . . . . ?
C11 C12 C13 C14 99.01(17) . . . . ?
C5 C12 C13 C14 -81.64(18) . . . . ?
C18 C13 C14 C15 1.0(2) . . . . ?
C12 C13 C14 C15 178.91(14) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 F1 -179.34(16) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
F1 C16 C17 C18 179.44(17) . . . . ?
C15 C16 C17 C18 -0.4(3) . . . . ?
C14 C13 C18 C17 -1.0(3) . . . . ?
C12 C13 C18 C17 -178.84(16) . . . . ?
C16 C17 C18 C13 0.6(3) . . . . ?
C12 C11 C19 C20 -67.22(18) . . . . ?
N1 C11 C19 C20 111.07(14) . . . . ?
C12 C11 C19 C24 109.59(16) . . . . ?
N1 C11 C19 C24 -72.13(17) . . . . ?
C24 C19 C20 C21 -0.8(2) . . . . ?
C11 C19 C20 C21 176.06(12) . . . . ?
C19 C20 C21 C22 0.7(2) . . . . ?
C20 C21 C22 F2 179.16(13) . . . . ?
C20 C21 C22 C23 0.0(2) . . . . ?
F2 C22 C23 C24 -179.65(13) . . . . ?
C21 C22 C23 C24 -0.5(2) . . . . ?
C20 C19 C24 C23 0.3(2) . . . . ?
C11 C19 C24 C23 -176.46(13) . . . . ?
C22 C23 C24 C19 0.3(2) . . . . ?
C8 C7 N1 N2 -1.93(19) . . . . ?
C6 C7 N1 N2 178.80(12) . . . . ?
C8 C7 N1 C11 177.75(12) . . . . ?
C6 C7 N1 C11 -1.52(18) . . . . ?
C12 C11 N1 N2 -178.49(12) . . . . ?
C19 C11 N1 N2 3.17(16) . . . . ?
C12 C11 N1 C7 1.79(18) . . . . ?
C19 C11 N1 C7 -176.54(11) . . . . ?
O1 C10 N2 N1 -178.61(12) . . . . ?
C9 C10 N2 N1 1.02(19) . . . . ?
C7 N1 N2 C10 0.90(19) . . . . ?
C11 N1 N2 C10 -178.80(11) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C25 H25^a O1 1.00 2.13 3.000(2) 144.4 . yes

_refine_diff_density_max         0.210
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.064

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_VA759_0m
_database_code_depnum_ccdc_archive 'CCDC 2548012'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2026-04-21 deposited with the CCDC.	2026-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2025/1
_shelx_SHELXL_version_number     2025/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H15 F N2 O, 0.354(H2 O)'
_chemical_formula_sum            'C24 H15.71 F N2 O1.35'
_chemical_formula_weight         372.76

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.1194(17)
_cell_length_b                   16.274(4)
_cell_length_c                   12.513(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.163(7)
_cell_angle_gamma                90
_cell_volume                     1822.0(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6353
_cell_measurement_theta_min      2.503
_cell_measurement_theta_max      28.031

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_F_000             774
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7131
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS 3.0'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III C14'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.391
_diffrn_reflns_number            17005
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0456
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.598
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_full        24.991
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3196
_reflns_number_gt                2708
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX5 (Bruker, 2023)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0496P)²+0.3078P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2025/1 (Sheldrick 2025)'
_refine_ls_extinction_coef       0.0113(19)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3196
_refine_ls_number_parameters     280
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1047
_refine_ls_wR_factor_gt          0.0987
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.60714(13) 0.64528(7) 0.71715(10) 0.0449(3) Uani 1 1 d . . . . .
C2 C 0.70664(14) 0.60246(7) 0.67072(10) 0.0459(3) Uani 1 1 d . . . . .
C3 C 0.67592(14) 0.58477(8) 0.55593(10) 0.0489(3) Uani 1 1 d . . . . .
C4 C 0.77321(18) 0.53745(10) 0.50630(13) 0.0641(4) Uani 1 1 d . . . . .
H4 H 0.860679 0.516572 0.548216 0.077 Uiso 1 1 calc R U . . .
C5 C 0.7401(2) 0.52195(11) 0.39694(14) 0.0763(5) Uani 1 1 d . . . . .
H5 H 0.804172 0.489906 0.364906 0.092 Uiso 1 1 calc R U . . .
C6 C 0.6103(2) 0.55415(11) 0.33334(13) 0.0741(5) Uani 1 1 d . . . . .
H6 H 0.589481 0.543995 0.258797 0.089 Uiso 1 1 calc R U . . .
C7 C 0.51361(18) 0.60014(9) 0.37843(11) 0.0619(4) Uani 1 1 d . . . . .
H7 H 0.428032 0.621465 0.334569 0.074 Uiso 1 1 calc R U . . .
C8 C 0.54262(15) 0.61564(8) 0.49162(10) 0.0490(3) Uani 1 1 d . . . . .
C9 C 0.44251(14) 0.66318(8) 0.54192(10) 0.0475(3) Uani 1 1 d . . . . .
C10 C 0.30823(16) 0.69899(10) 0.48409(12) 0.0607(4) Uani 1 1 d . . . . .
H10 H 0.280337 0.691443 0.409240 0.073 Uiso 1 1 calc R U . . .
C11 C 0.22190(17) 0.74353(10) 0.53718(13) 0.0654(4) Uani 1 1 d . . . . .
H11 H 0.133908 0.766403 0.498676 0.078 Uiso 1 1 calc R U . . .
C12 C 0.26281(15) 0.75667(9) 0.65275(12) 0.0562(4) Uani 1 1 d . . . . .
C13 C 0.62851(14) 0.65949(8) 0.83667(10) 0.0473(3) Uani 1 1 d . . . . .
C14 C 0.53891(16) 0.61821(9) 0.89702(11) 0.0576(4) Uani 1 1 d . . . . .
H14 H 0.460988 0.585376 0.861619 0.069 Uiso 1 1 calc R U . . .
C15 C 0.56433(19) 0.62542(11) 1.00934(12) 0.0680(4) Uani 1 1 d . . . . .
H15 H 0.503188 0.598481 1.049540 0.082 Uiso 1 1 calc R U . A 1
C17 C 0.77002(19) 0.71494(10) 1.00330(13) 0.0674(4) Uani 1 1 d . . . . .
H17 H 0.847974 0.747381 1.039537 0.081 Uiso 1 1 calc R U . B 1
C18 C 0.74294(16) 0.70879(9) 0.89042(12) 0.0565(4) Uani 1 1 d . . . . .
H18 H 0.802032 0.737973 0.850817 0.068 Uiso 1 1 calc R U . . .
C19 C 0.85146(14) 0.57548(8) 0.73948(10) 0.0470(3) Uani 1 1 d . . . . .
C20 C 0.86444(17) 0.50175(9) 0.79488(14) 0.0657(4) Uani 1 1 d . . . . .
H20 H 0.782559 0.466739 0.788146 0.079 Uiso 1 1 calc R U . . .
C21 C 0.99881(19) 0.47968(10) 0.86041(16) 0.0786(5) Uani 1 1 d . . . . .
H21 H 1.007861 0.429665 0.897050 0.094 Uiso 1 1 calc R U . C 1
C23 C 1.10947(15) 0.60466(9) 0.81534(12) 0.0587(4) Uani 1 1 d . . . . .
H23 H 1.192186 0.639063 0.822069 0.070 Uiso 1 1 calc R U . D 1
C24 C 0.97574(15) 0.62610(9) 0.74910(11) 0.0538(3) Uani 1 1 d . . . . .
H24 H 0.968842 0.675167 0.710355 0.065 Uiso 1 1 calc R U . . .
N1 N 0.47490(11) 0.67640(6) 0.65120(8) 0.0451(3) Uani 1 1 d . . . . .
N2 N 0.39067(12) 0.72167(7) 0.70862(9) 0.0526(3) Uani 1 1 d . . . . .
O1 O 0.18638(12) 0.79916(7) 0.70472(10) 0.0772(4) Uani 1 1 d . . . . .
C16 C 0.6813(2) 0.67302(11) 1.06023(12) 0.0696(5) Uani 0.547(3) 1 d . . P E 1
F1 F 0.7145(2) 0.67985(13) 1.16800(12) 0.0923(8) Uani 0.547(3) 1 d . . P E 1
C22 C 1.11812(17) 0.53185(10) 0.87094(14) 0.0682(4) Uani 0.547(3) 1 d . . P E 1
H22 H 1.207243 0.517562 0.916945 0.082 Uiso 0.547(3) 1 calc R U P E 1
C16D C 0.6813(2) 0.67302(11) 1.06023(12) 0.0696(5) Uani 0.453(3) 1 d . . P E 2
H16D H 0.700558 0.676745 1.135823 0.084 Uiso 0.453(3) 1 calc R U P E 2
C22D C 1.11812(17) 0.53185(10) 0.87094(14) 0.0682(4) Uani 0.453(3) 1 d . . P E
2
F1D F 1.2460(2) 0.51638(16) 0.9385(2) 0.1034(11) Uani 0.453(3) 1 d . . P E 2
O1W O -0.0174(5) 0.8431(3) 0.8257(5) 0.121(2) Uani 0.354(5) 1 d D . P . .
H1W H -0.084(8) 0.867(6) 0.779(6) 0.181 Uiso 0.354(5) 1 d D U P . .
H2W H 0.048(8) 0.835(6) 0.786(6) 0.181 Uiso 0.354(5) 1 d D U P . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.3603(17) . ?
C1 N1 1.4166(16) . ?
C1 C13 1.4885(18) . ?
C2 C3 1.4384(18) . ?
C2 C19 1.4958(17) . ?
C3 C4 1.4067(19) . ?
C3 C8 1.4139(19) . ?
C4 C5 1.367(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.359(2) . ?
C6 H6 0.9300 . ?
C7 C8 1.4123(19) . ?
C7 H7 0.9300 . ?
C8 C9 1.4320(19) . ?
C9 N1 1.3591(16) . ?
C9 C10 1.4211(19) . ?
C10 C11 1.337(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.438(2) . ?
C11 H11 0.9300 . ?
C12 O1 1.2500(18) . ?
C12 N2 1.3628(17) . ?
C13 C18 1.3833(19) . ?
C13 C14 1.389(2) . ?
C14 C15 1.384(2) . ?
C14 H14 0.9300 . ?
C15 C16D 1.371(2) . ?
C15 C16 1.371(2) . ?
C15 H15 0.9300 . ?
C17 C16D 1.360(3) . ?
C17 C16 1.360(3) . ?
C17 C18 1.390(2) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.379(2) . ?
C19 C24 1.3874(19) . ?
C20 C21 1.383(2) . ?
C20 H20 0.9300 . ?
C21 C22D 1.366(2) . ?
C21 C22 1.366(2) . ?
C21 H21 0.9300 . ?
C23 C22D 1.369(2) . ?
C23 C22 1.369(2) . ?
C23 C24 1.3800(19) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N1 N2 1.3649(15) . ?
C16 F1 1.328(2) . ?
C22 H22 0.9300 . ?
C16D H16D 0.9300 . ?
C22D F1D 1.325(3) . ?
O1W H1W 0.85(2) . ?
O1W H2W 0.86(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 119.82(11) . . ?
C2 C1 C13 122.71(11) . . ?
N1 C1 C13 117.45(10) . . ?
C1 C2 C3 120.80(11) . . ?
C1 C2 C19 119.49(11) . . ?
C3 C2 C19 119.69(11) . . ?
C4 C3 C8 119.31(12) . . ?
C4 C3 C2 122.20(12) . . ?
C8 C3 C2 118.49(12) . . ?
C5 C4 C3 120.47(15) . . ?
C5 C4 H4 119.8 . . ?
C3 C4 H4 119.8 . . ?
C4 C5 C6 120.05(15) . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C7 C6 C5 121.14(15) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 120.26(15) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
C7 C8 C3 118.74(13) . . ?
C7 C8 C9 121.71(13) . . ?
C3 C8 C9 119.53(12) . . ?
N1 C9 C10 116.45(12) . . ?
N1 C9 C8 119.66(11) . . ?
C10 C9 C8 123.89(12) . . ?
C11 C10 C9 120.09(14) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C10 C11 C12 121.13(13) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
O1 C12 N2 118.18(14) . . ?
O1 C12 C11 122.91(13) . . ?
N2 C12 C11 118.92(13) . . ?
C18 C13 C14 118.96(13) . . ?
C18 C13 C1 121.22(12) . . ?
C14 C13 C1 119.67(12) . . ?
C15 C14 C13 120.70(14) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C16D C15 C14 118.80(16) . . ?
C16 C15 C14 118.80(16) . . ?
C16 C15 H15 120.6 . . ?
C14 C15 H15 120.6 . . ?
C16D C17 C18 119.31(15) . . ?
C16 C17 C18 119.31(15) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C13 C18 C17 120.32(15) . . ?
C13 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C20 C19 C24 118.93(12) . . ?
C20 C19 C2 121.65(12) . . ?
C24 C19 C2 119.42(11) . . ?
C19 C20 C21 120.24(14) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 H20 119.9 . . ?
C22D C21 C20 119.56(15) . . ?
C22 C21 C20 119.56(15) . . ?
C22 C21 H21 120.2 . . ?
C20 C21 H21 120.2 . . ?
C22D C23 C24 118.78(14) . . ?
C22 C23 C24 118.78(14) . . ?
C22 C23 H23 120.6 . . ?
C24 C23 H23 120.6 . . ?
C23 C24 C19 120.94(13) . . ?
C23 C24 H24 119.5 . . ?
C19 C24 H24 119.5 . . ?
C9 N1 N2 125.47(10) . . ?
C9 N1 C1 121.62(11) . . ?
N2 N1 C1 112.87(10) . . ?
C12 N2 N1 117.93(11) . . ?
F1 C16 C17 116.63(18) . . ?
F1 C16 C15 121.50(19) . . ?
C17 C16 C15 121.87(14) . . ?
C21 C22 C23 121.51(14) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C17 C16D C15 121.87(14) . . ?
C17 C16D H16D 119.1 . . ?
C15 C16D H16D 119.1 . . ?
F1D C22D C21 121.96(18) . . ?
F1D C22D C23 116.48(18) . . ?
C21 C22D C23 121.51(14) . . ?
H1W O1W H2W 99(9) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -3.10(18) . . . . ?
C13 C1 C2 C3 175.15(11) . . . . ?
N1 C1 C2 C19 175.24(11) . . . . ?
C13 C1 C2 C19 -6.51(18) . . . . ?
C1 C2 C3 C4 -177.03(13) . . . . ?
C19 C2 C3 C4 4.64(19) . . . . ?
C1 C2 C3 C8 2.44(18) . . . . ?
C19 C2 C3 C8 -175.90(11) . . . . ?
C8 C3 C4 C5 0.5(2) . . . . ?
C2 C3 C4 C5 179.98(14) . . . . ?
C3 C4 C5 C6 1.0(3) . . . . ?
C4 C5 C6 C7 -1.0(3) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C6 C7 C8 C3 2.0(2) . . . . ?
C6 C7 C8 C9 -179.42(13) . . . . ?
C4 C3 C8 C7 -2.02(19) . . . . ?
C2 C3 C8 C7 178.50(11) . . . . ?
C4 C3 C8 C9 179.41(12) . . . . ?
C2 C3 C8 C9 -0.07(18) . . . . ?
C7 C8 C9 N1 179.89(11) . . . . ?
C3 C8 C9 N1 -1.59(18) . . . . ?
C7 C8 C9 C10 -0.5(2) . . . . ?
C3 C8 C9 C10 178.03(12) . . . . ?
N1 C9 C10 C11 0.6(2) . . . . ?
C8 C9 C10 C11 -179.07(13) . . . . ?
C9 C10 C11 C12 0.4(2) . . . . ?
C10 C11 C12 O1 178.65(15) . . . . ?
C10 C11 C12 N2 -1.1(2) . . . . ?
C2 C1 C13 C18 67.28(17) . . . . ?
N1 C1 C13 C18 -114.43(13) . . . . ?
C2 C1 C13 C14 -108.20(15) . . . . ?
N1 C1 C13 C14 70.09(15) . . . . ?
C18 C13 C14 C15 -0.7(2) . . . . ?
C1 C13 C14 C15 174.89(12) . . . . ?
C13 C14 C15 C16D -1.1(2) . . . . ?
C13 C14 C15 C16 -1.1(2) . . . . ?
C14 C13 C18 C17 1.77(19) . . . . ?
C1 C13 C18 C17 -173.74(12) . . . . ?
C16D C17 C18 C13 -1.1(2) . . . . ?
C16 C17 C18 C13 -1.1(2) . . . . ?
C1 C2 C19 C20 87.85(16) . . . . ?
C3 C2 C19 C20 -93.79(16) . . . . ?
C1 C2 C19 C24 -91.38(15) . . . . ?
C3 C2 C19 C24 86.98(15) . . . . ?
C24 C19 C20 C21 1.2(2) . . . . ?
C2 C19 C20 C21 -178.06(15) . . . . ?
C19 C20 C21 C22D 0.8(3) . . . . ?
C19 C20 C21 C22 0.8(3) . . . . ?
C22D C23 C24 C19 0.6(2) . . . . ?
C22 C23 C24 C19 0.6(2) . . . . ?
C20 C19 C24 C23 -1.9(2) . . . . ?
C2 C19 C24 C23 177.36(12) . . . . ?
C10 C9 N1 N2 -0.91(18) . . . . ?
C8 C9 N1 N2 178.73(11) . . . . ?
C10 C9 N1 C1 -178.67(11) . . . . ?
C8 C9 N1 C1 0.97(17) . . . . ?
C2 C1 N1 C9 1.39(18) . . . . ?
C13 C1 N1 C9 -176.95(11) . . . . ?
C2 C1 N1 N2 -176.62(11) . . . . ?
C13 C1 N1 N2 5.03(15) . . . . ?
O1 C12 N2 N1 -178.99(12) . . . . ?
C11 C12 N2 N1 0.80(19) . . . . ?
C9 N1 N2 C12 0.22(18) . . . . ?
C1 N1 N2 C12 178.15(11) . . . . ?
C18 C17 C16 F1 178.61(15) . . . . ?
C18 C17 C16 C15 -0.8(2) . . . . ?
C14 C15 C16 F1 -177.52(15) . . . . ?
C14 C15 C16 C17 1.9(2) . . . . ?
C20 C21 C22 C23 -2.1(3) . . . . ?
C24 C23 C22 C21 1.4(2) . . . . ?
C18 C17 C16D C15 -0.8(2) . . . . ?
C14 C15 C16D C17 1.9(2) . . . . ?
C20 C21 C22D F1D 175.2(2) . . . . ?
C20 C21 C22D C23 -2.1(3) . . . . ?
C24 C23 C22D F1D -176.01(19) . . . . ?
C24 C23 C22D C21 1.4(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1W H2W O1 0.86(2) 1.86(3) 2.711(5) 171(10) . yes

_refine_diff_density_max         0.130
_refine_diff_density_min         -0.127
_refine_diff_density_rms         0.025

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_mo_VA771_0m_a
_database_code_depnum_ccdc_archive 'CCDC 2548013'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2026-04-21 deposited with the CCDC.	2026-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2025/1
_shelx_SHELXL_version_number     2025/1
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H15 Cl N2 O, C H Cl3'
_chemical_formula_sum            'C25 H16 Cl4 N2 O'
_chemical_formula_weight         502.20

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.6258(17)
_cell_length_b                   14.1135(16)
_cell_length_c                   12.9741(17)
_cell_angle_alpha                90
_cell_angle_beta                 109.818(4)
_cell_angle_gamma                90
_cell_volume                     2347.2(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    6896
_cell_measurement_theta_min      2.206
_cell_measurement_theta_max      25.404

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             1024
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.160
_exptl_absorpt_coefficient_mu    0.525
_shelx_estimated_absorpt_T_min   0.902
_shelx_estimated_absorpt_T_max   0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6586
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Incoatec I\mS 3.0'
_diffrn_measurement_device_type  'Bruker D8 VENTURE PHOTON III C14'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean 7.391
_diffrn_reflns_number            26455
_diffrn_reflns_av_unetI/netI     0.0493
_diffrn_reflns_av_R_equivalents  0.0486
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.146
_diffrn_reflns_theta_max         28.380
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             5853
_reflns_number_gt                3570
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX5 (Bruker, 2023)'
_computing_cell_refinement       'SAINT (Bruker, 2019)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2019)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2019)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1133P)²+0.8933P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5853
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1027
_refine_ls_R_factor_gt           0.0705
_refine_ls_wR_factor_ref         0.2471
_refine_ls_wR_factor_gt          0.2200
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.38465(18) 0.37487(17) 0.5127(2) 0.0554(6) Uani 1 1 d . . . . .
C2 C 0.32134(19) 0.42459(18) 0.5534(2) 0.0584(6) Uani 1 1 d . . . . .
C3 C 0.3442(2) 0.43345(19) 0.6694(2) 0.0620(6) Uani 1 1 d . . . . .
C4 C 0.2809(3) 0.4864(2) 0.7149(3) 0.0801(8) Uani 1 1 d . . . . .
H4 H 0.222333 0.517621 0.668733 0.096 Uiso 1 1 calc R U . . .
C5 C 0.3044(3) 0.4923(3) 0.8246(3) 0.0929(11) Uani 1 1 d . . . . .
H5 H 0.261537 0.526883 0.853339 0.111 Uiso 1 1 calc R U . . .
C6 C 0.3918(3) 0.4472(3) 0.8943(3) 0.0892(10) Uani 1 1 d . . . . .
H6 H 0.407150 0.451919 0.969613 0.107 Uiso 1 1 calc R U . . .
C7 C 0.4561(3) 0.3958(2) 0.8546(3) 0.0784(8) Uani 1 1 d . . . . .
H7 H 0.514811 0.366175 0.902607 0.094 Uiso 1 1 calc R U . . .
C8 C 0.4332(2) 0.38798(19) 0.7403(2) 0.0616(6) Uani 1 1 d . . . . .
C9 C 0.4992(2) 0.33611(18) 0.6955(2) 0.0583(6) Uani 1 1 d . . . . .
C10 C 0.5905(2) 0.2870(2) 0.7595(2) 0.0700(7) Uani 1 1 d . . . . .
H10 H 0.609902 0.286697 0.835440 0.084 Uiso 1 1 calc R U . . .
C11 C 0.6486(2) 0.2414(2) 0.7108(3) 0.0728(8) Uani 1 1 d . . . . .
H11 H 0.708282 0.209606 0.753498 0.087 Uiso 1 1 calc R U . . .
C12 C 0.6208(2) 0.2406(2) 0.5943(2) 0.0619(6) Uani 1 1 d . . . . .
C13 C 0.36365(19) 0.36236(18) 0.3934(2) 0.0582(6) Uani 1 1 d . . . . .
C14 C 0.4219(3) 0.4079(2) 0.3401(2) 0.0739(8) Uani 1 1 d . . . . .
H14 H 0.479402 0.443936 0.379801 0.089 Uiso 1 1 calc R U . . .
C15 C 0.3954(3) 0.4002(3) 0.2284(3) 0.0898(10) Uani 1 1 d . . . . .
H15 H 0.434860 0.430938 0.192496 0.108 Uiso 1 1 calc R U . A 1
C17 C 0.2537(3) 0.3001(3) 0.2212(3) 0.0906(11) Uani 1 1 d . . . . .
H17 H 0.197460 0.262856 0.180938 0.109 Uiso 1 1 calc R U . B 1
C18 C 0.2797(2) 0.3078(2) 0.3328(3) 0.0746(8) Uani 1 1 d . . . . .
H18 H 0.240339 0.275951 0.368074 0.090 Uiso 1 1 calc R U . . .
C19 C 0.2266(2) 0.47249(19) 0.4770(2) 0.0621(6) Uani 1 1 d . . . . .
C20 C 0.2356(2) 0.5564(2) 0.4280(3) 0.0814(9) Uani 1 1 d . . . . .
H20 H 0.301208 0.583299 0.442409 0.098 Uiso 1 1 calc R U . . .
C21 C 0.1490(3) 0.6016(3) 0.3577(4) 0.0923(11) Uani 1 1 d . . . . .
H21 H 0.155973 0.659079 0.325792 0.111 Uiso 1 1 calc R U . C 1
C23 C 0.0417(2) 0.4781(3) 0.3838(3) 0.0885(10) Uani 1 1 d . . . . .
H23 H -0.024068 0.451462 0.368956 0.106 Uiso 1 1 calc R U . D 1
C24 C 0.1293(2) 0.4331(2) 0.4557(3) 0.0805(9) Uani 1 1 d . . . . .
H24 H 0.122049 0.376615 0.489236 0.097 Uiso 1 1 calc R U . . .
N1 N 0.47533(15) 0.33112(14) 0.58543(17) 0.0530(5) Uani 1 1 d . . . . .
N2 N 0.53240(16) 0.28544(16) 0.53264(18) 0.0592(5) Uani 1 1 d . . . . .
O1 O 0.67427(16) 0.19988(16) 0.54656(18) 0.0778(6) Uani 1 1 d . . . . .
C16 C 0.3109(3) 0.3473(3) 0.1702(3) 0.0913(11) Uani 0.579(3) 1 d . . P E 1
H16 H 0.292200 0.343621 0.094451 0.110 Uiso 0.579(3) 1 calc R U P E 1
C22 C 0.0526(2) 0.5611(3) 0.3354(3) 0.0824(9) Uani 0.579(3) 1 d . . P E 1
Cl1 Cl -0.05569(11) 0.61841(14) 0.24338(17) 0.1051(8) Uani 0.579(3) 1 d . . P E
1
C16D C 0.3109(3) 0.3473(3) 0.1702(3) 0.0913(11) Uani 0.421(3) 1 d . . P E 2
C22D C 0.0526(2) 0.5611(3) 0.3354(3) 0.0824(9) Uani 0.421(3) 1 d . . P E 2
H22D H -0.005884 0.590566 0.286701 0.099 Uiso 0.421(3) 1 calc R U P E 2
Cl1D Cl 0.2592(2) 0.33633(18) 0.03682(16) 0.1039(10) Uani 0.421(3) 1 d . . P E
2
C25 C 0.8759(3) 0.1612(3) 0.5044(3) 0.0900(10) Uani 1 1 d . . . . .
H25 H 0.815588 0.190927 0.516232 0.108 Uiso 1 1 calc R U . . .
Cl2 Cl 0.83016(14) 0.06276(11) 0.42411(15) 0.1531(6) Uani 1 1 d . . . . .
Cl3 Cl 0.92630(13) 0.24367(12) 0.43659(14) 0.1494(6) Uani 1 1 d . . . . .
Cl4 Cl 0.96360(12) 0.13435(14) 0.63167(14) 0.1617(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C2 1.350(4) . ?
C1 N1 1.417(3) . ?
C1 C13 1.487(4) . ?
C2 C3 1.436(4) . ?
C2 C19 1.497(4) . ?
C3 C8 1.404(4) . ?
C3 C4 1.413(4) . ?
C4 C5 1.352(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.365(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.412(4) . ?
C7 H7 0.9300 . ?
C8 C9 1.427(4) . ?
C9 N1 1.355(3) . ?
C9 C10 1.420(4) . ?
C10 C11 1.333(5) . ?
C10 H10 0.9300 . ?
C11 C12 1.428(4) . ?
C11 H11 0.9300 . ?
C12 O1 1.245(3) . ?
C12 N2 1.357(3) . ?
C13 C14 1.375(4) . ?
C13 C18 1.382(4) . ?
C14 C15 1.374(4) . ?
C14 H14 0.9300 . ?
C15 C16D 1.365(5) . ?
C15 C16 1.365(5) . ?
C15 H15 0.9300 . ?
C17 C16D 1.355(6) . ?
C17 C16 1.355(6) . ?
C17 C18 1.374(5) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.368(4) . ?
C19 C24 1.376(4) . ?
C20 C21 1.379(4) . ?
C20 H20 0.9300 . ?
C21 C22D 1.371(5) . ?
C21 C22 1.371(5) . ?
C21 H21 0.9300 . ?
C23 C22D 1.361(5) . ?
C23 C22 1.361(5) . ?
C23 C24 1.394(5) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N1 N2 1.360(3) . ?
C16 H16 0.9300 . ?
C22 Cl1 1.750(3) . ?
C16D Cl1D 1.640(4) . ?
C22D H22D 0.9300 . ?
C25 Cl4 1.721(4) . ?
C25 Cl2 1.721(4) . ?
C25 Cl3 1.735(4) . ?
C25 H25 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 N1 119.6(2) . . ?
C2 C1 C13 123.1(2) . . ?
N1 C1 C13 117.3(2) . . ?
C1 C2 C3 121.0(2) . . ?
C1 C2 C19 119.9(2) . . ?
C3 C2 C19 119.1(2) . . ?
C8 C3 C4 118.8(3) . . ?
C8 C3 C2 118.6(2) . . ?
C4 C3 C2 122.5(3) . . ?
C5 C4 C3 120.8(3) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 121.3(3) . . ?
C7 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C6 C7 C8 119.7(3) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 H7 120.1 . . ?
C3 C8 C7 119.1(3) . . ?
C3 C8 C9 119.4(2) . . ?
C7 C8 C9 121.5(3) . . ?
N1 C9 C10 116.1(2) . . ?
N1 C9 C8 119.8(2) . . ?
C10 C9 C8 124.1(3) . . ?
C11 C10 C9 120.1(3) . . ?
C11 C10 H10 119.9 . . ?
C9 C10 H10 119.9 . . ?
C10 C11 C12 121.2(3) . . ?
C10 C11 H11 119.4 . . ?
C12 C11 H11 119.4 . . ?
O1 C12 N2 118.3(3) . . ?
O1 C12 C11 122.8(3) . . ?
N2 C12 C11 118.9(3) . . ?
C14 C13 C18 118.8(3) . . ?
C14 C13 C1 121.9(2) . . ?
C18 C13 C1 119.2(3) . . ?
C15 C14 C13 120.2(3) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C16D C15 C14 119.8(4) . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C16D C17 C18 119.3(3) . . ?
C16 C17 C18 119.3(3) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 H17 120.3 . . ?
C17 C18 C13 120.7(3) . . ?
C17 C18 H18 119.6 . . ?
C13 C18 H18 119.6 . . ?
C20 C19 C24 119.2(3) . . ?
C20 C19 C2 120.3(2) . . ?
C24 C19 C2 120.4(3) . . ?
C19 C20 C21 121.0(3) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C22D C21 C20 119.4(3) . . ?
C22 C21 C20 119.4(3) . . ?
C22 C21 H21 120.3 . . ?
C20 C21 H21 120.3 . . ?
C22D C23 C24 119.9(3) . . ?
C22 C23 C24 119.9(3) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
C19 C24 C23 119.9(3) . . ?
C19 C24 H24 120.1 . . ?
C23 C24 H24 120.1 . . ?
C9 N1 N2 125.6(2) . . ?
C9 N1 C1 121.5(2) . . ?
N2 N1 C1 112.9(2) . . ?
C12 N2 N1 118.0(2) . . ?
C17 C16 C15 121.1(3) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C23 C22 C21 120.5(3) . . ?
C23 C22 Cl1 121.0(3) . . ?
C21 C22 Cl1 118.5(3) . . ?
C17 C16D C15 121.1(3) . . ?
C17 C16D Cl1D 110.9(3) . . ?
C15 C16D Cl1D 127.9(4) . . ?
C23 C22D C21 120.5(3) . . ?
C23 C22D H22D 119.7 . . ?
C21 C22D H22D 119.7 . . ?
Cl4 C25 Cl2 113.2(2) . . ?
Cl4 C25 Cl3 111.6(2) . . ?
Cl2 C25 Cl3 111.1(2) . . ?
Cl4 C25 H25 106.8 . . ?
Cl2 C25 H25 106.8 . . ?
Cl3 C25 H25 106.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -0.3(4) . . . . ?
C13 C1 C2 C3 179.0(2) . . . . ?
N1 C1 C2 C19 178.8(2) . . . . ?
C13 C1 C2 C19 -1.8(4) . . . . ?
C1 C2 C3 C8 -1.0(4) . . . . ?
C19 C2 C3 C8 179.8(2) . . . . ?
C1 C2 C3 C4 178.7(3) . . . . ?
C19 C2 C3 C4 -0.5(4) . . . . ?
C8 C3 C4 C5 -0.9(5) . . . . ?
C2 C3 C4 C5 179.3(3) . . . . ?
C3 C4 C5 C6 0.7(6) . . . . ?
C4 C5 C6 C7 -0.1(6) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C4 C3 C8 C7 0.5(4) . . . . ?
C2 C3 C8 C7 -179.7(2) . . . . ?
C4 C3 C8 C9 -178.5(3) . . . . ?
C2 C3 C8 C9 1.2(4) . . . . ?
C6 C7 C8 C3 0.1(4) . . . . ?
C6 C7 C8 C9 179.1(3) . . . . ?
C3 C8 C9 N1 -0.1(4) . . . . ?
C7 C8 C9 N1 -179.2(2) . . . . ?
C3 C8 C9 C10 -179.6(3) . . . . ?
C7 C8 C9 C10 1.4(4) . . . . ?
N1 C9 C10 C11 1.5(4) . . . . ?
C8 C9 C10 C11 -179.0(3) . . . . ?
C9 C10 C11 C12 -0.1(5) . . . . ?
C10 C11 C12 O1 178.9(3) . . . . ?
C10 C11 C12 N2 -1.4(4) . . . . ?
C2 C1 C13 C14 108.0(3) . . . . ?
N1 C1 C13 C14 -72.7(3) . . . . ?
C2 C1 C13 C18 -68.3(3) . . . . ?
N1 C1 C13 C18 111.1(3) . . . . ?
C18 C13 C14 C15 1.2(5) . . . . ?
C1 C13 C14 C15 -175.1(3) . . . . ?
C13 C14 C15 C16D 0.1(5) . . . . ?
C13 C14 C15 C16 0.1(5) . . . . ?
C16D C17 C18 C13 -0.5(5) . . . . ?
C16 C17 C18 C13 -0.5(5) . . . . ?
C14 C13 C18 C17 -0.9(5) . . . . ?
C1 C13 C18 C17 175.5(3) . . . . ?
C1 C2 C19 C20 -78.2(4) . . . . ?
C3 C2 C19 C20 101.0(3) . . . . ?
C1 C2 C19 C24 102.3(3) . . . . ?
C3 C2 C19 C24 -78.5(4) . . . . ?
C24 C19 C20 C21 -0.2(5) . . . . ?
C2 C19 C20 C21 -179.7(3) . . . . ?
C19 C20 C21 C22D -1.0(6) . . . . ?
C19 C20 C21 C22 -1.0(6) . . . . ?
C20 C19 C24 C23 0.9(5) . . . . ?
C2 C19 C24 C23 -179.6(3) . . . . ?
C22D C23 C24 C19 -0.4(6) . . . . ?
C22 C23 C24 C19 -0.4(6) . . . . ?
C10 C9 N1 N2 -1.6(4) . . . . ?
C8 C9 N1 N2 178.9(2) . . . . ?
C10 C9 N1 C1 178.2(2) . . . . ?
C8 C9 N1 C1 -1.3(3) . . . . ?
C2 C1 N1 C9 1.5(3) . . . . ?
C13 C1 N1 C9 -177.9(2) . . . . ?
C2 C1 N1 N2 -178.6(2) . . . . ?
C13 C1 N1 N2 1.9(3) . . . . ?
O1 C12 N2 N1 -178.9(2) . . . . ?
C11 C12 N2 N1 1.4(4) . . . . ?
C9 N1 N2 C12 0.1(3) . . . . ?
C1 N1 N2 C12 -179.7(2) . . . . ?
C18 C17 C16 C15 1.8(5) . . . . ?
C14 C15 C16 C17 -1.6(6) . . . . ?
C24 C23 C22 C21 -0.8(6) . . . . ?
C24 C23 C22 Cl1 179.1(3) . . . . ?
C20 C21 C22 C23 1.5(6) . . . . ?
C20 C21 C22 Cl1 -178.5(3) . . . . ?
C18 C17 C16D C15 1.8(5) . . . . ?
C18 C17 C16D Cl1D -174.4(3) . . . . ?
C14 C15 C16D C17 -1.6(6) . . . . ?
C14 C15 C16D Cl1D 174.0(3) . . . . ?
C24 C23 C22D C21 -0.8(6) . . . . ?
C20 C21 C22D C23 1.5(6) . . . . ?

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.052

